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According to recent Hollywood movies, the high school and college years are the time to get drunk, get laid, and—if you’re really lucky—get stalked by a homicidal maniac. Could it also be the time for moral education? That was the bold thesis of Amy Heckerling’s sparkling Clueless, which relocated Jane Austen’s Emma to an enchanted and yet convincingly contemporary California high school milieu. Despite sometimes borrowing plots from other classics, none of the teen movies that followed have taken Heckerling’s model to heart. Perhaps it’s harder than it looks, given that Heckerling, too, has now failed to observe Clueless’ precedent.

The writer-director’s latest moral tale, Loser, tries hard enough. It confronts big issues, turns an appealing young woman’s life around, and endeavors to be funny. Yet nearly everything about the film is a little off. Perhaps it’s because she has moved on to college—beginning with Fast Times at Ridgemont High, Heckerling has been most successful in high school—or because the college she selected (obviously based on NYU) is not in Southern California. Somewhere, Heckerling got lost.

Loser isn’t a disaster, but its charms are decidedly sporadic. This is a rare example of a recent Hollywood flick that starts unpromisingly and gradually becomes more winning; usually, it’s just the opposite. Still, a discussion of the film can only become a list of miscalculations.

The first is the character of Paul (American Pie’s Jason Biggs), the hero. A scholarship student from a place that’s so far upstate it seems to be in another era, Paul is smart, kind, and well-meaning. His only problem is a fashion sense that seems to have been formed in the Yukon territory. He has a haircut so dorky that it’s actually sort of hip and a fake-fur hat with flaps that pegs him as a rube. Because all that Paul really needs to learn in the course of the film is that he should get himself a cooler hat, there’s not much potential for self-discovery here.

The second is Paul’s relationship with his roommates (Thomas Sadoski, Zak Orth, and Jimmi Simpson), a trio of party animals who disdain the hard-studying, nonpartying country boy. These guys aren’t merely underage drinkers, blackmailers of professors, and players of dirty tricks. They are dispensers of “ropies,” date-rape drugs that sometimes kill. The reported vogue for such drugs is a subject worthy of cinematic consideration, but not in a light comedy. Heckerling devises end-credits comeuppances for the three villains, but they’re not enough. She shouldn’t have settled for anything less than 30-to-life.

The third is Paul’s unrequited love for classmate Dora (American Beauty’s Mena Suvari), a sorta-goth lit major who lives at home, a long commuter-train ride away. Dora is having an affair with brilliant but self-centered Professor Alcott (Greg Kinnear) and wears a leather bikini to work as a go-go-club bartender. (Her job would suggest that she’s over 21, yet she and Paul are in the same freshman-lit class.) Paul finds Dora unconscious after one of his despicable roomies slips her a ropie but apparently doesn’t rape her—that would be too rough for PG-13—and rushes her to the hospital to save her life. That Paul would be too shy to declare his passion for Dora is believable, but his noble attempts to actually further her romance with Alcott are more absurdly 19th-century than anything in Clueless.

The fourth problem is the celebration of Manhattan, which Paul and Dora explore together in a spirit of Woody Allenesque rapture. Dora, who subsists on a diet of honey from free condiments racks, shows her naive new pal how to freeload glamorously. They even sneak into a performance of Cabaret, complete with the original Broadway cast. Yet the whole thing seems phony, as if the film had mostly been shot in Toronto. (In fact, it was.)

The fifth, sixth, and seventh are the character of Alcott, too weaselly and openly selfish to be a successful seducer; the distracting and mostly unfunny bits by such comics as Dan Aykroyd, David Spade, Steven Wright, Andrea Martin, and others; and the tone-deaf use of music, including a gratuitous Everclear cameo and “Scarborough Fair/Canticle” as an ill-conceived nod to The Graduate.

The eighth is contemporary youth culture, with its careless hedonism, casual bigotry—”gay” is now slang for “lame”—and vicious narcissism. As depicted by Heckerling, today’s college campus is no place to stage a romantic comedy. Loser hopes you’ll laugh, you’ll cry…but instead you’ll want to call the police.

Nobody does the good old days like the British, so despite the fact that Thomas the Tank Engine didn’t get his own show until he was discovered by PBS, fans surely hoped that the plucky “really useful” steam engine’s big-screen debut would be made in the U.K. The Isle of Man counts, and Thomas and the Magic Railroad gets credit for filming there. Pennsylvania and Toronto (again) don’t, however, and neither do Peter Fonda, Alec Baldwin, and Mara Wilson, and all of those places and people appear, too.

Thomas and his pals, originally created in 1945 by the Rev. Wilber Awdry to entertain his seriously ill son, are the nicest bunch of steam engines you’ll ever meet. As envisioned by writer-director Britt Allcroft, who also created their TV incarnation, the locomotives are a little dull, but not nearly so mechanical as Baldwin (the pint-sized Mr. Conductor), Fonda (morose grandpa Burnett Stone), and Wilson (Lily, the little girl who restores magic to the town of Shining Time and the Island of Sodor, where trains have speaking parts). The members of the film’s Hollywood contingent act as if they’re talking to a special-effects screen even when delivering lines to each other.

The story is almost as complicated as it is uninteresting: Mr. Conductor is losing the magic that allows him to travel between Shining Time and Sodor, evil Diesel 10 is bedeviling Thomas and his steam-driven friends, Lily gets lost while visiting her grandfather, and Stone has a secret obsession that ties these subplots together. Thomas’ earnest determination to be “really useful” will no doubt warm the hearts of kindergarten teachers, but Allcroft was surely right to limit the tank engine’s original adventures to five-and-a-half-minute segments. There’s just not enough going on in Shining Time to merit a longer visit. CP